Hydrochloric Acid → 5-Nitronaphthalene-1,4-dione

HRID 1579670Notes

Reaction equation

HRID 1579670 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[C:12](=NO)[CH:11]=[CH:10][C:9]2=[O:16])([O-:3])=[O:2].Cl.[OH2:18]>O.O.O.O.[Fe](Cl)Cl>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[C:12](=[O:18])[CH:11]=[CH:10][C:9]2=[O:16])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178516261HCID 178516261, compound

Product 1

HCID 123364025-Nitronaphthalene-1,4-dione

Reagents, catalysts & solvents 1

HCID 16211588Ferrous chloride tetrahydrateCatalyst

Conditions

Temperature
40 °C

Procedure

42 g (0.21 mol) of iron (II) chloride tetrahydrate and 11 g (0.05 mol) of 8-nitro-1,4-naphthoquinone-1-oxime are introduced into 120 ml quantities of the solvents indicated in Table I below. While gaseous hydrogen chloride is slowly passed through them, the mixtures are left to react with continuous stirring at the temperatures indicated in Table I below until the respective reactions are complete. The increases in weight indicated in Table I below are obtained. After the reaction times specified in Table I, the mixtures are poured onto 500 ml of water heated to approximately 40°C, followed by stirring for 30 minutes. The 5-nitro-1,4-naphthoquinone formed is filtered off under suction, washed off under suction, washed with water until neutral and dried at 50°C. The yields of 5-nitro-1,4-naphthoquinone specified in Table I below in g and percent of the theoretical yield are obtained.

Workup

  1. waitthe mixtures are left
  2. customto react
  3. temperatureThe increases in weight
  4. custombelow are obtained
  5. customAfter the reaction times
  6. stirringby stirring for 30 minutes

Sources & evidence

ORD record
ord-ca2706cb0efb4efdbd1ad1c225711fc2
Source dataset
uspto-grants-1976_01
Patent number
US03931255

Reaction notes

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